N-[2-(4,6-Dimethoxy­pyrimidin-2-ylcarbon­yl)phen­yl]benzamide

Li, Y.; Huang, G.

doi:10.1107/S1600536807056553

N-[2-(4,6-Dimethoxypyrimidin-2-ylcarbonyl)phenyl]benzamide

Y. Li and G. Huang

In the molecule of the title compound, C₂₀H₁₇N₃O₄, intramolecular C—H

O and N—H

O hydrogen bonds result in the formation of two nearly planar six-membered rings; these are almost coplanar with the adjacent six-membered ring. In the crystal structure, C—H

O hydrogen bonds link the molecules.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807056553/hk2369sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807056553/hk2369Isup2.hkl Contains datablock I

CCDC reference: 672910

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Key indicators

Single-crystal X-ray study
T = 292 K
Mean (C-C) = 0.003 Å
R factor = 0.049
wR factor = 0.132
Data-to-parameter ratio = 13.6

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No syntax errors found



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   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
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Comment top

Pyrimidine derivatives have broad biological properties: in particular pyrimidinylbenzoate is a highly effective herbicide with acetohydroxy acid synthese (AHAS) as target (Duggleby et al., 2000). We report herein the crystal structure of one such pyrimidine derivative, the title compound, (I).

In the molecule of (I), (Fig. 1) the bond lengths and angles are generally within normal ranges (Allen et al., 1987). Rings A (C1—C6), B (C8—C13) and C (N2/N3/C15—C18) are, of course, planar and the dihedral angles between them are A/B = 16.40 (3)°, A/C = 87.51 (2)° and B/C = 87.15 (3)°. The intramolecular C—H···O and N—H···O hydrogen bonds (Table 1) result in the formation of the nearly planar six-membered rings; D (O1/N1/C7—C9/H9) and E (N1/O2/C8/C13/C14/H1A), which are oriented at a dihedral angle of D/E = 3.05 (2)°. They are also oriented with respect to ring B at dihedral angles of D/B = 2.60 (3)° and E/B = 0.94 (3)°. So, rings B, D and E are nearly co-planar.

In the crystal structure, intermolecular C—H···O hydrogen bonds (Table 1) link the molecules, in which they may be effective in the stabilization of the structure.

Related literature top

For general background, see: Duggleby et al. (2000). For related literature, see: Li et al. (2006). For bond-length data, see: Allen et al. (1987).

Experimental top

The title compound was synthesized according to the literature method (Li et al., 2006). Crystals appropriate for X-ray analysis were obtained by slow evaporation of the dichloromethane solution at 283 K.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL (Bruker, 2001).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A packing diagram of (I). Hydrogen bonds are shown as dashed lines.

N-[2-(4,6-Dimethoxypyrimidin-2-ylcarbonyl)phenyl]benzamide top

Crystal data top

C₂₀H₁₇N₃O₄	Z = 2
M_r = 363.37	F(000) = 380
Triclinic, P1	D_x = 1.339 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.7723 (10) Å	Cell parameters from 1758 reflections
b = 9.9453 (13) Å	θ = 2.6–26.4°
c = 11.8667 (16) Å	µ = 0.10 mm⁻¹
α = 95.774 (2)°	T = 292 K
β = 91.581 (2)°	Block, colorless
γ = 98.657 (2)°	0.30 × 0.20 × 0.10 mm
V = 901.4 (2) Å³

Data collection top

Bruker SMART 4K CCD area-detector diffractometer	2340 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.048
Graphite monochromator	θ_max = 25.8°, θ_min = 2.1°
ϕ and ω scans	h = −9→9
5032 measured reflections	k = −10→12
3386 independent reflections	l = −14→14

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.132	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	w = 1/[σ²(F_o²) + (0.0701P)²] where P = (F_o² + 2F_c²)/3
3386 reflections	(Δ/σ)_max < 0.001
249 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₂₀H₁₇N₃O₄	γ = 98.657 (2)°
M_r = 363.37	V = 901.4 (2) Å³
Triclinic, P1	Z = 2
a = 7.7723 (10) Å	Mo Kα radiation
b = 9.9453 (13) Å	µ = 0.10 mm⁻¹
c = 11.8667 (16) Å	T = 292 K
α = 95.774 (2)°	0.30 × 0.20 × 0.10 mm
β = 91.581 (2)°

Data collection top

Bruker SMART 4K CCD area-detector diffractometer	2340 reflections with I > 2σ(I)
5032 measured reflections	R_int = 0.048
3386 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.132	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	Δρ_max = 0.24 e Å⁻³
3386 reflections	Δρ_min = −0.23 e Å⁻³
249 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.61486 (19)	0.38351 (18)	1.17647 (12)	0.0971 (6)
O2	0.21277 (16)	0.18961 (15)	0.85457 (10)	0.0768 (4)
O4	0.3427 (2)	0.17339 (15)	0.42123 (10)	0.0792 (4)
O3	0.08396 (19)	−0.23710 (14)	0.53910 (11)	0.0800 (4)
N1	0.44601 (19)	0.28284 (14)	1.02392 (11)	0.0507 (4)
H1A	0.343 (2)	0.2783 (17)	0.9827 (14)	0.061*
N2	0.33883 (19)	0.14925 (15)	0.61258 (11)	0.0587 (4)
N3	0.2033 (2)	−0.06098 (16)	0.67381 (12)	0.0594 (4)
C1	0.3827 (2)	0.56041 (18)	1.23623 (14)	0.0571 (5)
H1	0.4963	0.5807	1.2667	0.069*
C2	0.2605 (3)	0.63962 (19)	1.27421 (15)	0.0650 (5)
H2	0.2919	0.7125	1.3301	0.078*
C3	0.0936 (3)	0.6111 (2)	1.22983 (16)	0.0687 (5)
H3	0.0112	0.6646	1.2551	0.082*
C4	0.0476 (3)	0.5030 (2)	1.14772 (16)	0.0695 (6)
H4	−0.0662	0.4832	1.1176	0.083*
C5	0.1699 (2)	0.42366 (19)	1.10982 (15)	0.0618 (5)
H5	0.1378	0.3507	1.0542	0.074*
C6	0.3393 (2)	0.45170 (16)	1.15385 (13)	0.0486 (4)
C7	0.4798 (2)	0.37067 (18)	1.11999 (14)	0.0541 (4)
C8	0.5518 (2)	0.19496 (16)	0.97185 (13)	0.0474 (4)
C9	0.7138 (2)	0.18155 (19)	1.01697 (15)	0.0597 (5)
H9	0.7550	0.2307	1.0857	0.072*
C10	0.8143 (2)	0.0960 (2)	0.96084 (17)	0.0668 (5)
H10	0.9235	0.0896	0.9919	0.080*
C11	0.7570 (2)	0.0197 (2)	0.85983 (16)	0.0648 (5)
H11	0.8260	−0.0382	0.8232	0.078*
C12	0.5967 (2)	0.03076 (18)	0.81442 (14)	0.0561 (5)
H12	0.5568	−0.0210	0.7465	0.067*
C13	0.4912 (2)	0.11829 (16)	0.86788 (13)	0.0472 (4)
C14	0.3246 (2)	0.12940 (18)	0.81204 (14)	0.0536 (4)
C15	0.2867 (2)	0.06568 (19)	0.69021 (14)	0.0532 (4)
C16	0.2977 (2)	0.09688 (19)	0.50574 (14)	0.0587 (5)
C17	0.2109 (2)	−0.03313 (19)	0.47669 (14)	0.0603 (5)
H17	0.1835	−0.0681	0.4016	0.072*
C18	0.1669 (2)	−0.10860 (19)	0.56526 (15)	0.0592 (5)
C19	0.4327 (4)	0.3102 (2)	0.4506 (2)	0.1002 (8)
H19A	0.3609	0.3618	0.4967	0.150*
H19B	0.4578	0.3531	0.3827	0.150*
H19C	0.5397	0.3070	0.4920	0.150*
C20	0.0442 (4)	−0.3184 (2)	0.6325 (2)	0.0977 (8)
H20A	0.1505	−0.3274	0.6723	0.146*
H20B	−0.0152	−0.4075	0.6036	0.146*
H20C	−0.0289	−0.2743	0.6834	0.146*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0690 (9)	0.1285 (14)	0.0882 (10)	0.0411 (9)	−0.0227 (8)	−0.0468 (10)
O2	0.0624 (8)	0.1085 (12)	0.0605 (8)	0.0368 (8)	−0.0032 (6)	−0.0203 (7)
O4	0.1189 (12)	0.0693 (9)	0.0483 (7)	0.0105 (8)	0.0106 (7)	0.0050 (6)
O3	0.1021 (11)	0.0630 (9)	0.0675 (8)	−0.0029 (8)	−0.0023 (8)	−0.0035 (7)
N1	0.0500 (8)	0.0582 (9)	0.0447 (8)	0.0176 (7)	−0.0005 (6)	−0.0035 (7)
N2	0.0677 (10)	0.0595 (9)	0.0484 (8)	0.0126 (8)	0.0045 (7)	−0.0016 (7)
N3	0.0642 (9)	0.0607 (10)	0.0520 (9)	0.0102 (8)	0.0001 (7)	−0.0001 (7)
C1	0.0637 (11)	0.0525 (11)	0.0546 (10)	0.0106 (9)	0.0024 (8)	0.0007 (8)
C2	0.0840 (14)	0.0514 (11)	0.0607 (11)	0.0191 (10)	0.0084 (10)	−0.0040 (9)
C3	0.0798 (14)	0.0671 (13)	0.0664 (12)	0.0331 (11)	0.0154 (11)	0.0068 (10)
C4	0.0605 (11)	0.0857 (15)	0.0644 (11)	0.0243 (11)	0.0044 (9)	−0.0014 (11)
C5	0.0579 (11)	0.0681 (12)	0.0580 (11)	0.0148 (9)	0.0024 (9)	−0.0077 (9)
C6	0.0541 (10)	0.0484 (10)	0.0438 (9)	0.0092 (8)	0.0053 (7)	0.0041 (7)
C7	0.0516 (10)	0.0620 (11)	0.0479 (9)	0.0127 (9)	−0.0003 (8)	−0.0037 (8)
C8	0.0501 (10)	0.0482 (10)	0.0468 (9)	0.0146 (8)	0.0076 (7)	0.0071 (7)
C9	0.0594 (11)	0.0635 (12)	0.0587 (10)	0.0206 (9)	−0.0005 (8)	0.0019 (9)
C10	0.0593 (11)	0.0704 (13)	0.0749 (13)	0.0267 (10)	−0.0008 (9)	0.0032 (11)
C11	0.0665 (12)	0.0612 (12)	0.0743 (13)	0.0319 (10)	0.0155 (10)	0.0068 (10)
C12	0.0647 (11)	0.0536 (11)	0.0522 (10)	0.0168 (9)	0.0115 (8)	0.0026 (8)
C13	0.0524 (10)	0.0470 (10)	0.0437 (9)	0.0117 (8)	0.0094 (7)	0.0042 (7)
C14	0.0549 (10)	0.0582 (11)	0.0479 (9)	0.0134 (9)	0.0070 (8)	−0.0018 (8)
C15	0.0526 (10)	0.0616 (12)	0.0465 (9)	0.0175 (9)	0.0031 (8)	−0.0025 (8)
C16	0.0697 (12)	0.0592 (12)	0.0495 (10)	0.0197 (10)	0.0050 (8)	0.0014 (9)
C17	0.0755 (13)	0.0638 (12)	0.0421 (9)	0.0201 (10)	0.0022 (8)	−0.0062 (8)
C18	0.0622 (11)	0.0570 (11)	0.0570 (11)	0.0134 (9)	−0.0013 (9)	−0.0059 (9)
C19	0.139 (2)	0.0753 (16)	0.0820 (15)	−0.0038 (15)	0.0033 (15)	0.0188 (13)
C20	0.120 (2)	0.0714 (15)	0.0945 (17)	−0.0124 (14)	0.0013 (14)	0.0169 (13)

Geometric parameters (Å, º) top

C1—C6	1.378 (2)	C12—C13	1.402 (2)
C1—C2	1.379 (2)	C12—H12	0.9300
C1—H1	0.9300	C13—C14	1.462 (2)
C2—C3	1.365 (3)	C14—O2	1.2202 (19)
C2—H2	0.9300	C14—C15	1.521 (2)
C3—C4	1.374 (3)	C15—N3	1.320 (2)
C3—H3	0.9300	C15—N2	1.333 (2)
C4—C5	1.381 (2)	C16—N2	1.333 (2)
C4—H4	0.9300	C16—O4	1.341 (2)
C5—C6	1.381 (2)	C16—C17	1.371 (2)
C5—H5	0.9300	C17—C18	1.374 (2)
C6—C7	1.492 (2)	C17—H17	0.9300
C7—O1	1.213 (2)	C18—N3	1.334 (2)
C7—N1	1.359 (2)	C18—O3	1.344 (2)
C8—C9	1.385 (2)	C19—O4	1.438 (3)
C8—N1	1.399 (2)	C19—H19A	0.9600
C8—C13	1.413 (2)	C19—H19B	0.9600
C9—C10	1.375 (2)	C19—H19C	0.9600
C9—H9	0.9300	C20—O3	1.450 (2)
C10—C11	1.377 (3)	C20—H20A	0.9600
C10—H10	0.9300	C20—H20B	0.9600
C11—C12	1.368 (2)	C20—H20C	0.9600
C11—H11	0.9300	N1—H1A	0.920 (18)

C6—C1—C2	121.09 (18)	C12—C13—C14	118.55 (15)
C6—C1—H1	119.5	C8—C13—C14	122.58 (14)
C2—C1—H1	119.5	O2—C14—C13	125.05 (15)
C3—C2—C1	120.00 (18)	O2—C14—C15	116.24 (15)
C3—C2—H2	120.0	C13—C14—C15	118.68 (14)
C1—C2—H2	120.0	N3—C15—N2	128.16 (15)
C2—C3—C4	119.81 (18)	N3—C15—C14	117.58 (15)
C2—C3—H3	120.1	N2—C15—C14	114.22 (16)
C4—C3—H3	120.1	N2—C16—O4	119.32 (17)
C3—C4—C5	120.17 (19)	N2—C16—C17	123.23 (17)
C3—C4—H4	119.9	O4—C16—C17	117.45 (16)
C5—C4—H4	119.9	C16—C17—C18	115.92 (16)
C4—C5—C6	120.57 (18)	C16—C17—H17	122.0
C4—C5—H5	119.7	C18—C17—H17	122.0
C6—C5—H5	119.7	N3—C18—O3	119.44 (17)
C1—C6—C5	118.36 (16)	N3—C18—C17	123.41 (18)
C1—C6—C7	117.05 (15)	O3—C18—C17	117.15 (16)
C5—C6—C7	124.58 (15)	O4—C19—H19A	109.5
O1—C7—N1	122.95 (16)	O4—C19—H19B	109.5
O1—C7—C6	120.97 (16)	H19A—C19—H19B	109.5
N1—C7—C6	116.07 (15)	O4—C19—H19C	109.5
C9—C8—N1	122.86 (16)	H19A—C19—H19C	109.5
C9—C8—C13	118.79 (15)	H19B—C19—H19C	109.5
N1—C8—C13	118.34 (14)	O3—C20—H20A	109.5
C10—C9—C8	120.46 (17)	O3—C20—H20B	109.5
C10—C9—H9	119.8	H20A—C20—H20B	109.5
C8—C9—H9	119.8	O3—C20—H20C	109.5
C9—C10—C11	121.61 (17)	H20A—C20—H20C	109.5
C9—C10—H10	119.2	H20B—C20—H20C	109.5
C11—C10—H10	119.2	C7—N1—C8	128.87 (15)
C12—C11—C10	118.78 (17)	C7—N1—H1A	119.9 (11)
C12—C11—H11	120.6	C8—N1—H1A	111.2 (11)
C10—C11—H11	120.6	C16—N2—C15	114.66 (16)
C11—C12—C13	121.51 (17)	C15—N3—C18	114.62 (15)
C11—C12—H12	119.2	C16—O4—C19	117.99 (15)
C13—C12—H12	119.2	C18—O3—C20	117.02 (15)
C12—C13—C8	118.85 (15)

C6—C1—C2—C3	−0.2 (3)	C8—C13—C14—C15	167.82 (15)
C1—C2—C3—C4	0.3 (3)	O2—C14—C15—N3	−89.3 (2)
C2—C3—C4—C5	−0.2 (3)	C13—C14—C15—N3	92.49 (19)
C3—C4—C5—C6	0.1 (3)	O2—C14—C15—N2	88.6 (2)
C2—C1—C6—C5	0.0 (3)	C13—C14—C15—N2	−89.62 (19)
C2—C1—C6—C7	−178.89 (15)	N2—C16—C17—C18	0.2 (3)
C4—C5—C6—C1	0.0 (3)	O4—C16—C17—C18	180.00 (15)
C4—C5—C6—C7	178.87 (16)	C16—C17—C18—N3	0.5 (3)
C1—C6—C7—O1	13.4 (3)	C16—C17—C18—O3	−179.04 (16)
C5—C6—C7—O1	−165.47 (18)	O1—C7—N1—C8	−0.6 (3)
C1—C6—C7—N1	−166.98 (15)	C6—C7—N1—C8	179.81 (14)
C5—C6—C7—N1	14.2 (2)	C9—C8—N1—C7	2.6 (3)
N1—C8—C9—C10	−178.44 (16)	C13—C8—N1—C7	−176.46 (16)
C13—C8—C9—C10	0.6 (3)	O4—C16—N2—C15	179.28 (15)
C8—C9—C10—C11	−1.1 (3)	C17—C16—N2—C15	−0.9 (3)
C9—C10—C11—C12	0.5 (3)	N3—C15—N2—C16	1.1 (3)
C10—C11—C12—C13	0.5 (3)	C14—C15—N2—C16	−176.49 (15)
C11—C12—C13—C8	−0.9 (2)	N2—C15—N3—C18	−0.6 (3)
C11—C12—C13—C14	177.38 (16)	C14—C15—N3—C18	176.99 (15)
C9—C8—C13—C12	0.4 (2)	O3—C18—N3—C15	179.21 (15)
N1—C8—C13—C12	179.46 (14)	C17—C18—N3—C15	−0.3 (3)
C9—C8—C13—C14	−177.85 (15)	N2—C16—O4—C19	−0.5 (3)
N1—C8—C13—C14	1.2 (2)	C17—C16—O4—C19	179.61 (18)
C12—C13—C14—O2	171.58 (16)	N3—C18—O3—C20	−2.1 (3)
C8—C13—C14—O2	−10.2 (3)	C17—C18—O3—C20	177.45 (18)
C12—C13—C14—C15	−10.4 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O1	0.93	2.21	2.826 (2)	123
N1—H1A···O2	0.920 (18)	1.868 (18)	2.6651 (18)	143.6 (15)
C12—H12···O4ⁱ	0.93	2.59	3.374 (2)	142

Symmetry code: (i) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₇N₃O₄
M_r	363.37
Crystal system, space group	Triclinic, P1
Temperature (K)	292
a, b, c (Å)	7.7723 (10), 9.9453 (13), 11.8667 (16)
α, β, γ (°)	95.774 (2), 91.581 (2), 98.657 (2)
V (Å³)	901.4 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Bruker SMART 4K CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	5032, 3386, 2340
R_int	0.048
(sin θ/λ)_max (Å⁻¹)	0.611

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.132, 0.98
No. of reflections	3386
No. of parameters	249
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.23

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXTL (Bruker, 2001).